1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[g]-2-benzopyran → Benzopyran

HRID 2217120Notes

Reaction equation

HRID 2217120 reaction equation
C[CH:2]1[C:7]2[CH:8]=[C:9]3C(C)(C)C(C)C(C)(C)[C:10]3=[CH:11][C:6]=2[CH2:5][O:4][CH2:3]1>C(O)C>[O:4]1[C:3]2[CH:2]=[CH:7][CH:8]=[CH:9][C:10]=2[CH:11]=[CH:6][CH2:5]1

Participants

3

Reactant 1

HCID 914971,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[g]-2-benzopyran

Product 1

HCID 9211Benzopyran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

200 grams of the liquid phase benzopyran mixture was prepared according to Example 15 of U.S. Pat. No. 3,360,530 containing 78% by weight of 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta[G]-2-benzopyran and 100 grams of 10% aqueous ethanol were admixed and cooled to a temperature of +5° C. with stirring. Stirring continued for a period of 2 hours at which point in time solid particles began to precipitate. The mixture was stirred for an additional 3 hours at 5° C. 42 grams of white crystalline material were filtered at 5° C. The resulting composition was a solid phase benzopyran mixture containing 91 weight % of 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[G]-2-benzopyran having a melting point of 31° C.

Workup

  1. temperaturecooled to a temperature of +5° C.
  2. stirringStirring
  3. customto precipitate
  4. stirringThe mixture was stirred for an additional 3 hours at 5° C
  5. filtration42 grams of white crystalline material were filtered at 5° C
  6. additioncontaining 91 weight % of 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[G]-2-benzopyran having a melting point of 31° C.

Sources & evidence

ORD record
ord-7115415402ec4594aee4bab163fdd91a
Source dataset
uspto-grants-2008_08
Patent number
US07407928B2

Reaction notes

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